Family-friendly vacation rentals in Olean

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Olean

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Superhost

The cottage exterior features a stone façade, complemented by a welcoming porch and large windows. Greenery surrounds the entrance, with potted plants adding a touch of life. The front door, framed by glass panels, offers a glimpse into the cozy interior.

Cottage in Olean

4.83 out of 5 average rating, 183 reviews

Artists cottage - mid century

The perfect spot to relax, read, write meditate. View birds, wildlife in an old forest along the Allegany River from the porch, deck or large picture windows. Take a walk. (fast Wi Fi, 32 inch TV and echo dot) Families and dog owners will like the large yard (no fence, warning ticks and Lyme disease in the area). My grandmother designed the cottage around a vintage house trailer (tiny house)1956. There are many unique and cleaver features. Family mementos through history are on display.

Superhost

A warm living space features a stone fireplace with a flickering fire. A bottle of red wine rests on a wooden table, accompanied by two wine glasses. Nearby, a festive candle is set atop a decorative tray, contributing to a cozy atmosphere.

Chalet in Swain

4.88 out of 5 average rating, 404 reviews

Chalet- Letchworth and Stony Brook State Parks 50%

Visiting Swain ski Mountain Resort is truly a wonderful experience. This open space with private lodge like feeling is fantastic for a romantic getaway or for a vacation with family and friends. Immerse yourself in the beauty of the outdoors within the exquisite state land of upstate New York. Just 15 miles from Letchworth State Park. 12 miles from Stony Brook State park. Rattle Snake State Park is just a block away. If you love adventure and the outdoors this is the perfect place!

Guest favorite

The living area features wooden walls and flooring, creating a rustic ambiance. A comfortable seating arrangement includes a sofa and chairs. A wooden table sits nearby. A staircase leads to the upper level. Wall-mounted decorations enhance the natural theme, including mounted animal displays.

Cabin in Almond

4.95 out of 5 average rating, 291 reviews

The Country Cabin

Quiet, peaceful, and private cabin in the woods. Explore 4000 acres of State Land nearby. Hiking, nature walks, or birdwatching. Enjoy cross-country skiing on the nearby state land. Relax by the pond, fish, or take a refreshing swim. Tall Pines ATV Park (11 miles) offers off-road adventures. Hit the slopes at Swain Ski Resort (22 miles) for winter sports. Located near SUNY Alfred and AU (2 Miles), ideal for parents visiting. Perfect for a family vacation or a weekend getaway.

Top guest favorite

Home in Ellicottville

4.97 out of 5 average rating, 105 reviews

Windsor Castle - Cozy Farmhouse Ellicottville

Windsor Castle - Your Cozy Ski & Golf Retreat Escape to serenity at Windsor Castle, a charming 2,300 sq ft farmhouse nestled on four rolling acres in Ellicottville. This beautifully restored 1900s home perfectly blends rustic charm with modern comfort, featuring a tranquil 3/4-acre pond that mirrors the changing seasons. Minutes from Western New York's premier ski destinations and golf courses, this private retreat offers the perfect balance of seclusion and accessibility.

Top guest favorite

A modern kitchen features sleek black and white cabinetry, complemented by a dark countertop. A round wall art piece adds character, while a door leads to an exterior space. Large windows provide natural light, and essential appliances are neatly integrated into the design.

Apartment in Chaffee

4.98 out of 5 average rating, 131 reviews

The Hidden Gem - West

This brand new renovated 2 bedroom 1 bath duplex is the perfect place to stay, whether your visiting family in Western NY or just visiting to enjoy all of the beauty of our great state. All brand new appliances, washer and dryer and central AC to keep you cool in the hot summer months. We are approximately 30 minutes from Holiday Valley for some great skiing, just off the snowmobile trail for some great snowmobiling and the ATV and SXS trails are popping up all around us.

Guest favorite

A welcoming living room is featured with two comfortable sofas positioned around a rustic wooden coffee table. A stone fireplace adds warmth to the space, complemented by a flat-screen TV mounted above. Large curtains frame the door leading to the balcony, allowing natural light to filter in.

Townhouse in Ellicottville

4.94 out of 5 average rating, 153 reviews

Alpine Retreat- Bottom of ski hill, gorgeous view

Slope-side bliss awaits at this townhouse near Sunrise lift. Just a 4-min drive or 15-min walk to a vibrant town with shops, dining, and events. Pet/smoke-free, it offers high-speed WiFi, Roku TV, a cozy fireplace, AC, and new washer/dryer. The deck boasts Muskoka chairs and scenic views. Your perfect mountain escape! You'll love the vibe and access to the hill and golf course. We're a Super-Host and aim to provide exceptional value.

Guest favorite

The living area features a light-toned sofa and armchair, complemented by decorative cushions. A wooden coffee table sits in front of the seating, with a small potted plant atop it. Large windows provide natural light, while a dining area with a dark wooden table is visible in the background.

Apartment in Ellicottville

4.81 out of 5 average rating, 113 reviews

Apartment with AC, close to Ellicottville village

Beautiful, modern 2 bedroom/1 bathroom apartment perfect for a getaway with friends or a fun family weekend! **25% off for WEEKLY bookings** Equipped with all of the amenities of home including linens, kitchen wares, gas fireplace, washer and dryer and a TV in each room. Pull-out couch creates enough room for 6 people to stay. Located only 1 mile from the quaint Village of Ellicottville and 2 miles from the slopes!

Top guest favorite

A well-lit bathroom features a wooden vanity with sink and storage drawers. A mirror with warm lighting is mounted above the sink. A shower area is partially enclosed by a maroon curtain, and a soft rug lies on the tiled floor.

Home in Ellicottville

4.96 out of 5 average rating, 155 reviews

Stay in style. Walk to everything!

Sure to be your favorite for visits to come! Enjoy this beautiful home with large kitchen, nice & comfortable furniture, and newer carpet throughout. Relax on the back deck or front porch. Off-street parking. WiFi. Go head-to-head on our air hockey or shuffleboard tables. Take a short walk to the heart of town! Perfect for time with spa weekends, golf outings, ski season, family, and more. Rentals are 30 days+.

Guest favorite

A small log cabin is presented featuring an inviting front porch with a railing. Solar panels are visible on the roof. The surrounding area includes greenery and a gravel pathway, contributing to the rural setting.

Cabin in Great Valley

4.91 out of 5 average rating, 309 reviews

The Porcupine, featuring fiber optic internet

* Get Away From it all The Porcupine is a small, comfortable and private log cabin. And and we are proud to be solar powered! Great for a couple or a family with small children. Rural setting great for hikes or bikes. 3 miles to the village of Ellicottville. 8 miles to the Seneca Allegany Casino. And 2 miles to the slopes of Holiday Valley

Superhost

The exterior of a two-story duplex is presented, featuring light grey siding and a warm red front door. A small porch area with a decorative wreath is visible, alongside neatly trimmed bushes and open green lawn space, enhancing the inviting atmosphere of the home.

Home in Kane

4.86 out of 5 average rating, 341 reviews

Charming Half Duplex Side 1

Charming home in friendly neighborhood. Perfect for a couple guests, or groups up to 6. Friends and family oriented, with 2 queen bedrooms, 1 bunkbed room, and a sleeper sofa. All amenities for a comfortable stay are included! Close to the newly blossoming downtown Kane, the Kinzua Reservoir, Kinzua Bridge State park, the Allegheny National Forest, and the Knox Kane Rail Trail is just a block away!

Top guest favorite

A charming wooden cabin is nestled among trees, with a welcoming front porch and an American flag waving gently. A circular fire pit surrounded by four adirondack chairs is centrally located on a well-maintained green lawn, with smoke rising softly into the air.

Cabin in Dalton

4.97 out of 5 average rating, 140 reviews

Upscale Cozy Cabin in the Woods-LETCHWORTH

20 MINUTES FROM LETCHWORTH STATE PARK. WiFi - High-Speed Internet -No Pets (Team member is allergic to animals) -No Smoking -No shoes worn inside cabin -No cutting down live or dead trees -No use of WOOD BURNING STOVE -No parties, events of any kind, and additional guests other than those listed in your reservation are not permitted without our prior approval. Check In: 3PM Check Out: 11AM

Guest favorite

A light-filled living area features large windows framed by soft curtains, revealing views of the surrounding forest. A comfortable sofa and a fold-out couch provide seating, while a low coffee table holds a decorative bowl and a magazine. Warm, neutral tones enhance the serene atmosphere.

Apartment in Great Valley

4.88 out of 5 average rating, 262 reviews

Cozy apartment tucked into the forest (with sauna)

Nestled in the forest only seven minutes’ drive from Holiday Valley, this contemporary style self-contained apartment is the perfect weekend getaway for skiing and nature-loving couples. With every luxury and convenience including a sauna, you can home cook meals or barbecue on the deck, with nothing but forest beyond, relax and watch a movie on our LCD screen or use high speed Starlink internet.

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What guests are saying

Walk to weddings, concerts, mountian fun. Air/con

4.84 out of 5 average rating, 94 reviews2 months ago

When visiting Holiday Valley for some skiing this ski-in, ski-out accommodation is absolutely perfect! Our group has been staying here for a view years and the place never disappoints. The kitchen is well stocked and the living space is very comfortable. Looking forward to our next opportunity to stay here.

Townhouse in Ellicottville

What guests are saying

Steps to town. Close to all activities.

4.84 out of 5 average rating, 80 reviews8 months ago

Frances's place was amazing! We felt right at home with everything we needed (extra towels, wine glasses, ice trays, etc.). Couldn't have asked for a better location with downtown just a 5 minute walk away and both ski hills nearby too. Would definitely recommend this home!

Home in Ellicottville

What guests are saying

Perfect place to stay - Ellicottville

4.95 out of 5 average rating, 75 reviews3 months ago

This home was absolutely perfect for our weekend getaway! The location was fantastic, right in the heart of Ellicottville with easy access to everything we wanted to see. The space itself was spotless, beautifully decorated, and had everything we needed for a comfortable stay. Mike was incredibly responsive and helpful. We would definitely stay here again!

Home in Ellicottville

What guests are saying

Cozy waterfront cottage, Rushford Lake, NY

4.83 out of 5 average rating, 24 reviews32 months ago

Our second time at this great location! The house and property are in the perfect spot, peaceful with a great waterfront setting. So nice to relax in the hammock and take in the view, or walk to the beach nearby. Everything we needed, and more, was provided. It is so great to have access to the kayaks, too! Thanks again, Toni Marie!

Cottage in Caneadea

What guests are saying

Ellicottville Vacation Rental

4.96 out of 5 average rating, 28 reviews3 months ago

We so enjoyed our stay at this lovely home . The house was spotless and very accommodating for our needs . The beds were great and the living room area warm and comfortable. The kitchen area is huge and plenty of seating at the table / counter space . The area was close enough to slopes and town . Beautiful view from back windows . Joseph , the host, is the best by far we have encountered. He is friendly, communicative and we appreciated his flexibility for us . We look very much forward to returning to Joseph’s home ! Thank you !

Home in Ellicottville

What guests are saying

EVL Acres - 13 acres & 3 minutes to village!

4.92 out of 5 average rating, 142 reviews1 month ago

We booked Chris' location based on the ratings and because we knew the area we wanted to stay in. By chance, the house was available for the dates we were interested in, as it was pretty booked on other days. Chris was very helpful, promptly answering our calls and assisting whenever needed. Realistically, we had no issues, but knowing we had a responsive and accommodating host was reassuring. The house closely matched the description. It’s a great place to stay for a few days if you’re looking to explore the area, go skiing, hiking, or enjoy other activities. While not brand new, it was clean, functional, and everything (water, heating, etc.) worked as expected—no issues at all. Overall, we were very satisfied with our stay. The price was very fair, and a 5-star rating is well deserved!

Home in Ellicottville

What guests are saying

Lake front home in Sunset Bay NY

4.85 out of 5 average rating, 48 reviews6 months ago

This was our second visit. My friends and I had a great time. Rob called us to make sure all was good!! We are planning a stay hopefully for September 2025. Beach was beautiful… house was nice and comfortable for the four of us. Loved having a bedroom for each of us!! Rob, thank you for sharing your home.

Home in Irving

What guests are saying

Shaker of Salt at Rushford Lake

4.61 out of 5 average rating, 23 reviews5 months ago

We stayed at the lake house for 3 days in November for deer hunting in the area, 4 of us were comfortable in the large cabin. Place was super clean & everything Kathleen described about the place was how we found it. The only issue we had was GPS led us down the wrong trail road. It was our own fault & Kathleen answered our call promptly & directed us to the proper trail road. Would definitely stay here again, for either a hunting trip or summertime getaway. Five stars!

Cottage in Caneadea

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